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Winston
Winston is the lead quantitative analyst at Taylor Mason Capital. Season 3 A Generation Too Late Winston interviews for a position at Axe Capital. He fails the box test given to him and Taylor tells him that he although he is a genius, he unable to control his emotional state. Icebreaker Taylor and Winston meet after his math meetup, where Winston tells them he's glad that they gave him a call and that he's re-evaluated himself since the interview. Taylor offers him the job if he promises not to be rude. Winston promises to try and Taylor gives him an address to go to. At the location, he finds Taylor and two other quants in a basement, where they all agree to start working on an algorithm for Taylor. Kompenso Taylor arrives to the basement to find that the other two quants have left because Winston insulted them. They keep Winston on as the sole quant since he is talented enough to handle all the work, despite his attitude. Taylor then asks him questions about the current state of the algorithm and its ability before leaving again. Winston shows Taylor the completed algorithm and reassures them that it will perform well and Taylor compliments him on his good work. Season 4 Chickentown Taylor calls in Winston and Mafee into their office to explain why they're not making as much money as expected. Winston says that costs were higher than anticipated by the algorithm, to which Mafee says that they are being front run. Winston then says that he thought it was strange but didn't inform anyone. Fight Night Winston, Sara, Lauren, and Mafee are in a meeting with Taylor to discuss the fracking legalization decision. Mafee remarks that he has not seen Taylor act so cold and openly vindictive before, to which Winston says that he's also never seen them screw over their father before. Taylor agrees with him, saying that although they weren't this way by nature, they have been forced to become this way and will not stop until they take down Axe. Later, they all gather around a TV when Axe is on, lying about the circumstances of Taylor leaving Axe Capital and their character. Taylor then calls into the show to dispute some of the lies. Axe bets Taylor that Dollar Bill will beat Mafee in their boxing match later that day. After the fight ending in a draw, Winston is the only one happy, as he was the only one who had bet on that being the outcome. He exclaims that he is a winner. Lamster Taylor announces to their employees that it is compensation time, but that they will only receive their full amount if they leave their money in the fund for the next year. They are all displeased with this announcement. Winston, Lauren, and Mafee are discussing the compensation situation when Taylor walks in, asking what the issue is. Winston then goes on a rant where he tells them that they are pressuring them into not receiving their full payment and that if they cannot afford to pay everyone in full, they should just pay their most valuable workers first. He then goes on to compare Taylor's actions to Axe's and criticize them for putting their revenge plot ahead of their workers. Mafee comes to Taylor's defense, telling Winston he should be more loyal to Taylor and that if he didn't like how they ran their company, then he could leave and start his own. He then states that he has already chosen to leave his money in the fund and that it was time for Winston to make a choice. Winston reluctantly defers and leaves his money, too. Extreme Sandbox Taylor takes what Winston said about their actions being similar to Axe's to heart and announces that they will no longer be focusing on their revenge plot, much to Winston's and the rest of the employee's pleasure. Taylor is then approached by Chuck, who tells them about his and Axe's plot to take them down. He convinces them to work with him to bring Axe down once and for all. Axe then thinks he blackmails Taylor into working for him again. Winston, Taylor, Lauren, Sara, and Mafee then arrive at Axe Capital, ready to work at their new office.